3-Bromo-1,1,1-Trifluoro-2-Propanol → 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[3,3,3-trifluoro-2-(7-methoxy-quinoxalin-2-yloxy)-propyl]-piperidin-4-yl}-amide

HRID 1019879Notes

Reaction equation

HRID 1019879 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:15][CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18].C(O[C:27](=[O:35])[NH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(C)(C)C.[O:36]=[C:37]1[NH:42][C:41]2[CH:43]=[C:44](C(O)=O)[CH:45]=[CH:46][C:40]=2[S:39][CH2:38]1>>[F:18][C:17]([F:20])([F:19])[CH:16]([O:21][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[N:3]=1)[CH2:15][N:32]1[CH2:31][CH2:30][CH:29]([NH:28][C:27]([C:44]2[CH:45]=[CH:46][C:40]3[S:39][CH2:38][C:37](=[O:36])[NH:42][C:41]=3[CH:43]=2)=[O:35])[CH2:34][CH2:33]1

Participants

5

Reactant 4

HCID 2206323-Bromo-1,1,1-Trifluoro-2-PropanolHCID 7238334-(N-Boc-amino)piperidineHCID 7609933-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acidHCID 126864152-Chloro-7-methoxyquinoxaline

Product 1

HCID 468522303-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid {1-[3,3,3-trifluoro-2-(7-methoxy-quinoxalin-2-yloxy)-propyl]-piperidin-4-yl}-amide

Procedure

The title compound is prepared as an off-white lyophilizated powder following Scheme 1 and in analogy to Example 1 using 2-chloro-7-methoxy-quinoxaline, 3-bromo-1,1,1-trifluoro-2-propanol, piperidin-4-yl-carbamic acid tert-butyl ester and 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid as starting materials.

Sources & evidence

ORD record
ord-895ba464cac7434183fcec9ceefbf2b1
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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